Grammys 2008

Both Joan Jett and Hilary Duff got their start as teens, Jett as a "jailbait rocker" in seventies punk band The Runaways, and Duff, well, on the Disney Channel. Still, how better for Duff to follow a trailblazer than in classic Converse? "I remember thinking, 'I hope one day people don't look at women like they're out of their minds when they want to pick up an instrument and play," Jett has said. "And I think we're getting a lot closer to that."